Chiral spaces: dissymmetric capsules through self-assembly.
Molecules with self-complementary surfaces interact through weak intermolecular forces to form assemblies, and the assembled states frequently exhibit distinctive properties. Described here are systems in which symmetrical molecules assemble through hydrogen bonding to produce capsules with dissymmetric cavities. The capsules form and dissipate on a time scale that permits their direct observation by nuclear magnetic resonance measurements, and they act as hosts for smaller molecular guests. Molecular recognition of chiral guests, such as naturally occurring terpenes, determines which dissymmetric cavities are preferentially formed in the assembly process.
Rivera
J M
JM
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Martín
T
T
Rebek
J
J
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D019281:Dimerization; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry*; D013816:Thermodynamics
D019086:Bridged Bicyclo Compounds, Heterocyclic; D013388:Succinimides